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Antimicrobial spiroketal macrolides and dichloro-diketopiperazine from Micromonospora sp. FIMYZ51.
- Source :
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Fitoterapia [Fitoterapia] 2024 Jun; Vol. 175, pp. 105946. Date of Electronic Publication: 2024 Apr 02. - Publication Year :
- 2024
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Abstract
- Four compounds (1-4) featuring with an <subscript>L</subscript> -rhodinose and spiroketal, possess uncommon continuous hydroxy groups in the macrolide skeleton, and a dichloro-diketopiperazine (5) were isolated from a marine derived Micromonospora sp. FIMYZ51. The determination of the relative and absolute configurations of all isolates was achieved by extensive spectroscopic analyses, single-crystal X-ray diffraction analysis, and ECD calculations. According to structural characteristic and genomic sequences, a plausible biosynthetic pathway for compound 1-4 was proposed and a spirocyclase was inferred to be responsible for the formation of the rare spirocyclic moiety. Compounds 1-4 exhibited potent antifungal activities which is equal to itraconazole against Aspergillus niger. Compounds 1-5 exhibited different degree of inhibitory activities against opportunistic pathogenic bacteria of endocarditis (Micrococcus luteus) with MIC values ranging from 0.0625 μg/mL to 32 μg/mL. Compounds 2 and 3 showed moderate cytotoxicity against drug-resistant tumor cell lines (Namalwa and U266). The result not only provides active lead-compounds, but also reveal the potential of the spirocyclase gene resources from Micromonospora sp., which highlights the promising potential of the strain for biomedical applications.<br />Competing Interests: Declaration of competing interest There are no conflicts to declare.<br /> (Copyright © 2023. Published by Elsevier B.V.)
- Subjects :
- Molecular Structure
Cell Line, Tumor
Humans
Anti-Bacterial Agents pharmacology
Anti-Bacterial Agents isolation & purification
Anti-Bacterial Agents chemistry
Antifungal Agents pharmacology
Antifungal Agents isolation & purification
Antifungal Agents chemistry
Microbial Sensitivity Tests
China
Antineoplastic Agents pharmacology
Antineoplastic Agents isolation & purification
Antineoplastic Agents chemistry
Furans
Diketopiperazines pharmacology
Diketopiperazines isolation & purification
Diketopiperazines chemistry
Micromonospora
Spiro Compounds pharmacology
Spiro Compounds isolation & purification
Spiro Compounds chemistry
Macrolides pharmacology
Macrolides isolation & purification
Macrolides chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1873-6971
- Volume :
- 175
- Database :
- MEDLINE
- Journal :
- Fitoterapia
- Publication Type :
- Academic Journal
- Accession number :
- 38575087
- Full Text :
- https://doi.org/10.1016/j.fitote.2024.105946